Lawyers From Around The World Share Cases They Regret Winning

Lawyers From Around The World Share Cases They Regret Winning

At some point in their careers, every lawyer will end up defending a bad guy. If they do their jobs right, they'll win, even if they don't want to. Same goes for unfair worker's compensation cases, ugly divorces, custody trials, and malevolent insurance companies. We asked lawyers from around the world to share the cases they regret winning. These courtroom successes will haunt them - and us - for a lifetime.


37. Money does horrible things to people.

We settled a case for several million dollars for a girl whose father was accidentally killed. The mother (who was divorced from the father) tried every way possible to get the money, but it was placed into a blocked account until the girl turned 18.

The DAY she turned 18, mom told her they were going to transfer the money to a "better account." Mom transferred it to her own account and fled the country WITHOUT the daughter. Screwed her own kid over for money, and essentially made her kid an orphan.

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36. It's not the dog's fault.

Family law is a little different in that you never really "win" per se. You may get more favorable rulings or better terms, but unless the opposing party did something illegal or mindbogglingly stupid it's never a decisive "win" really. Although I did have a case where my client fought really hard for the dog, and then ended up turning him over to a shelter. What a piece of work. The ex-wife received an "anonymous" tip and was able to get him back quickly.

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35. Too much of a good thing.

As a personal injury attorney, I've seen a few clients win the "blue collar lotto" or getting more money than they reasonably know how to deal with. I do my best to educate them, but my job is to try and maximize their recovery, not teach them finance. I have definitely contributed to a few bad habits, because they inevitably drink it all away, or gamble, or worse.

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34. Fate is unpredictable.

This is a strange one. Had a client where the Crown was seeking 3-4 months jail. Judge for some reason takes sympathy on this guy with a bad record and gives him a fine. Serious charge but the facts were not particularly egregious and there was no minimum sentence. Did my submissions make a difference? Perhaps. A month or two later later, I find out he died accidentally. If he had gone to jail, he might still be alive.

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33. Should have lost on purpose.

When I was a young associate, I was assigned to do a civil commercial trial for a client that was not happy with the senior partner. He stopped paying. We moved to withdraw. The court refused to allow us to withdraw and forced us to go to trial. Spend a significant amount of time in trial prep., etc. I win the trial. Client never pays (client's position was that my boss screwed up the deal and that there never should have been a dispute/trial to begin with). Firm policy prohibits us from suing clients because that causes a drastic increase in malpractice premiums - 9 times out of 10 if you sue a client for nonpayment, they will countersue for malpractice.


32. Provoked beyond reason.

Prosecuted a murder case. Twenty one year old kid starts dating an older guy's ex-girlfriend. The older guy (real roughneck, loose connections with a local biker gang) was going all over his small town talking about how he was going to beat the kid up. The older guy sends some nudes of the ex, so the kid says something smart in response. Older guy comes to the kid's house to fight him. The kid shoots him once, and the older guy dies. Jury didn't buy self-defense or castle doctrine. Convicted of voluntary manslaughter. Twenty years. Burned up his appeals with no luck.

I have a son about the kid's age. I could totally imagine him doing the exact same things if he were in a similar situation. It's going to haunt me until I die. No doubt about it. Started thinking about other work the moment the verdict came back.

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31. Get lost in legalese.

There was a case that I saw that involved a claim with fee shifting - meaning that if the plaintiff won, their attorneys’ fees would get paid by the defendant. Defendant pushed an aggressive legal position at trial that the judge agreed with, and won, avoiding a few thousand in liability to the plaintiff and a few thousand in attorneys’s fees. So far so good. But then the plaintiff appeals all the way to the state’s high court, requiring a ton of briefing and time. High court agrees with plaintiff, reverses and sends back to the trial court, which now enters judgement against the defendant for a few thousand in damages against the plaintiff and tens and tens of thousands of dollars in attorneys’ fees from the appeal. The defense lawyer probably regretted winning at first on that aggressive argument to the trial court.

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30. Insurance companies are the worst.

Guy lost his wife and children in a car accident. He wanted to exercise to get his emotions and mental health back in check. Doctor wrote him recommendations for exercise equipment (ball, chin up bar, nothing crazy) and he submitted the expenses for same to his insurer.

Client (insurer/adjuster) wanted this fought tooth and nail because exercise equipment was only covered for physical rehab and he was not physically injured.

I do not practice in this area anymore.

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29. Maybe you are jinxed.

Had this happen to me twice. Got my client out on bail only to thereafter have him up and killed. First time, he was in building supposedly selling, got chased by the police and a struggle ensued where he was shot point blank in the head. Mother told me that it was my fault that he was killed and that I was working with the DA and the police.

Second time, a young man no more then 16 gets released while waiting trial on robbery. One of the conditions of release was that he maintain a curfew. That very night he breaks curfew goes over to somebody else’s house and was killed in a robbery. Mother blamed me and said that the devil was working through me that we were all demons.

Criminal defense is a hard business.


28. Family court justice.

I did some custody work early in my career and won some cases more on the merit of my trial skills than on the merit of the parents. The thing with family law work in general is that there is essentially no bar to entry - anybody with a law degree and a pulse can get a family law practice up and running quickly because there is just an absolute glut of work. What that also means is that 75%+ of the lawyers practicing family law are clueless and awful. Early in my career I certainly was clueless, but at the least I was not awful. Therefore, in a battle between clueless+awful versus just clueless, clueless usually won.

So yeah, I can't recall any specific cases, except to say that fighting over children in court is a terrible thing and basically everyone loses. I regret that entire portion of my career.

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27. Less than the sum of its parts.

I won a summary judgment motion, that my firm filed not expecting to win. We had a decent argument, but odds were way worse than a coin flip and judges don't like granting summary judgment because it's an extreme remedy.

Basically, in a summary judgment you file a motion asking the judge to review all the facts (not a trial and not with witnesses, it's all done on paper, reviewing expert reports or witnesses's under oath deposition testimony taken usually months prior) and ask the judge to say, "yes all these things are true, but it is not enough to show a violation of the law, party filing the motion wins."

And you do not proceed to a trial. Do not pass go. Do not collect your contingency fee. (that's a lawyer joke...a contingency fee is what sometimes winning lawyers get paid only when they win.

Client initially was thrilled--"case is over"--we tried to break the news gently...nope. Three years later we're back in the same spot we were before we "won" our motion. The other side appealed it up to the state supreme court and won (because the Supreme Court said the trial judge should have denied our motion). So, we are back at square one. North of $100k in legal bills, with no resolution. Maybe it'll settle, maybe it will go to trial. I'll find out in the next 3-4 months.

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26. Didn't want to chase that ambulance.

I wouldn't say I regret this so much as to this day it amazes me. As a first year associate I was given a (terrible) personal injury case where my client received a flu shot and thereafter felt pain in his shoulder. He went to another doctor who performed an MRI and determined he had a torn rotator cuff, which was undoubtedly not related. My job was to allege the flu shot caused the rotator cuff tear. Our ortho actually correlated the two (which is the more regrettable position) and the case paid out.

Being the bottom of the totem pole I had no choice but to take the case, which was handed down by a partner. But at the same time, just overwhelmingly made me feel like the worst stereotyped attorney and just hated having to walk into court on it and feel my reputation being destroyed.


25. Malpractice every day.

I work in medical malpractice defense. Once I had a obstetrician/gynecologist who burned a patient during a procedure. When I met with the doctor, he lied to me throughout the representation over 16 months saying he had no idea how it happened. There is a doctrine in law called "res ipsa" meaning absent some sort of negligence, this accident could not have occurred.

Woman came in without a burn, and after the procedure, the woman left with a burn. There's no way this doctor didn't know what had happened. The area of the burn was where he was operating on. It wasn't until I brought up settlement, because this was not a case we could win did he say, "oh maybe I do know what happened." We ultimately settled that case, which is considered a favorable outcome considering the potential high monetary verdict. Sometimes I think this doctor really ought to have lost that case and their license.

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24. Money does buy something.

I got a spoiled brat of a teenager cleared of a shoplifting charge when he absolutely had done it. His rich parents hired me to represent him, I did that to the best of my ability, and we went to trial and won, but I can't say I felt good about it. This kid needed to be taught some accountability for his actions and his parents just wanted to buy their way out of any trouble he got into.

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23. Life's not fair.

I’m a work comp attorney. Now I represent injured people, but used to work on the other side, in insurance defense.

There was an applicant with a serious injury. Fell off a ladder, busted back with fusion, shoulder ruined, years of treatment. Internal issues, psych issues - really just all-round messed up. 50%+ permanent disability. We were 5 years in and finally getting to settlement time. If we bought out his future medical, settlement pretty far into 6 figures. This guy was the sole provider for wife and 2 kids.

Then we found out he had a aggressive brain cancer. Expected only couple years to live, at best. Thus, we wouldn’t buy out future medical anymore. Still got permanent disability for $60k-ish... but can’t give medical buyout based on 25+ year life expectancy anymore.

I felt terrible for the guy and his family. Me and the adjuster tried to get insurance to agree to some sort of amount like 5 year buyout, but the bean counters said no. The attorney knew it wasn’t me making the decision. Even though he worked on that guy’s file for 5+ years he decided to take $0 in fees. I have so much respect for that attorney turning down $10k+ in fees to help his client in a very bad situation.

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22. The family that sues together, stays together.

I do family law and I represented a father who had lost most of his custody from substance use and imprisonment as a result. He came to me saying he was clean and doing good and had his life together and it checked out. He had been clean for almost nine months not counting jail time and seemed sincere in wanting to resume a full relationship with his son. The other side fought viciously to keep him at extremely little custody and supervised at that, but we prevailed and got an order restoring fairly frequent unsupervised partial custody.

Not long afterwards, only about three months after the case, he was back to being an addict, sold most of his furniture, and for me the most soul-crushing is that he set up a fake GoFundMe stuff for his child's "cancer" (his child didn't have cancer and has never had cancer so you know where that money was going). I withdrew my appearance at this point so I don't know what happened afterwards, but I imagine and hope his custody was taken away.

Basically the net result of winning that case was that the poor boy had to witness his father relapse and was exploited for money. Worst case I ever won.

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21. Out of the frying pan, into the fire.

I had this one case that I still think about a lot. Worked in criminal defense, represented a guy in a DUI. He had priors, so another conviction meant time, loss of license, problems. Long story short, he was pulled over by police after they followed him leaving a bar. At trial I elicited admissions from the arresting officer that during the 2.5 miles he followed him for, he did not observe a single moving violation - no speeding, erratic driving, driving over the lines, blowing stop signs, running red lights. Didn’t even “stop suddenly” at red lights. Also got the DRE officer to testify that the accused only spoke Spanish and they couldn’t get an interpreter officer to the roadside to explain the field sobriety exercises, which the officers documented the accused “refused to perform.” Jury came back in 15 minutes. Guy was extremely grateful, and his lovely family was very gracious in thanking me and our office. Feel good about the whole thing.

Couple months later I’m in county to meet with a client, and I see him in one of the pods. Find out sometime after the trial he violently beat his 8 year old step-daughter.


20. One night of fun, a lifetime of regret.

Shadowed on a personal injury case. Their client was drinking in one of our guy's bars and gets wasted, becomes abusive to staff and then storms out, falls down the stairs. C6 ASIA B incomplete spinal injury- severe loss of mobility and sensation. His people sue and we force them to accept contributory negligence and personal liability. He gets an okay payout that covers his legal fees and immediate needs and is left disabled. Even if it was seen to be his fault it was still hard thinking that his life will never be the same just because of one rowdy night. Spinal injury care is massively expensive and the money he received wouldn't be sufficient for his whole life.

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19. Stop letting her off.

The one I particularly hated happened at my first law job. This woman was a long term client of my boss. In the past ten years or so, she has been caught driving under the influence 8 times, violated home incarceration countless times, been caught with controlled substances a few times, and stabbed two people on home incarceration. My boss at the time was the master of getting people off for DUI’s so she had only been convicted of a DUI third and always managed to stay on home incarceration with whatever releases she desired. I always regretted her cases because that woman is truly a danger to the public. She’s undoubtedly going to kill someone someday. But I’ll be damned if she isn’t the luckiest woman alive in getting away with DUIs.


18. Hard to feel bad for the guy.

Guy was a convicted felon so couldn’t be in possession of any firearms. He pawned 2 guns that were traced back to him by the pawn shop paperwork (he said they were his and put his thumbprint on the papers, also had store clerk say he walked in carrying them). His story was that his girlfriend’s mom found them after her father died (they were his) and wanted to get rid of them. So girlfriend (also convicted felon) asked him to help sell them, which he did.

DA office refused to waive the 3-year min man prison sentence, so it went to trial. I was the prosecutor when it went and ultimately got a guilty, the guy had to do 3 years day for day. I felt bad because I think his story was true, but he had a conviction for armed robbery and battery from 30 years ago so that was why the office wouldn’t agree to reduce the sentence.

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17. Divorce is never easy.

I represented this construction worker in a divorce. The wife stayed at home with the kids and had no money. Through entire divorce her attorney claimed that my client was hiding money. They had no evidence and the client vehemently denied it.

We had a good settlement in the case and I considered it done. When the client came in a few weeks later to pick up his file he thanked me for my work and said “and she never did find the money I hid” he had a big laugh and walked away.

What a jerk.

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16. Looking for room and board.

First few months of my career, my employer had me do public defense to get courtroom experience. And so it happened that as a clueless 25 year old, I had to defend Mr. Alfred (not the real name) against domestic violence against the woman he had been living with. From the outset, I should say he was innocent and you would think so too. The prosecutor shouldn’t have tried it, but basically just wanted to test the newbie, me.

So there I am, on a sub-zero January day, faking my way through a jury trial. I should note, I had met Mr. Alfred one time, a week prior. He shows up for his trial in the same dirty clothes and thin jacket as the week before. We didn’t know if there would be a trial until the afternoon before. A long day of trying my hardest to keep this stranger out of jail. Finally, we finish, the case is given to the jury for deliberations. In 10 minutes they deliver a not guilty verdict. Elation and relief for me. Shook Mr. Alfred’s hand, and he shuffled back out to the street, still homeless. In retrospect he would have been better off in jail for a few months.

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15. Caught on tape.

Not really “winning” but I recently had a case settle where my client was so obviously lying it was painful. He was in a fender bender and said he was too disabled to drive or to work at the office as a result, and that his employer fired him after he had been on disability leave for almost a year. A few months after filing, we discovered that he played in a national, amateur, full-contact football league and there was footage of him getting tackled, endzone dancing, and tackling during the time he claimed he was too hurt to sit at a desk. Even when I confronted him on it, he claimed he hadn’t played while he was injured—despite having a stat line and footage of him playing from games dated on days he was supposedly getting physical therapy.

We didn’t settle for as much as most of my cases but he still walked away with like $20k. I’m happy to be a plaintiff’s attorney for the most part because my clients have typically been wronged but he was such a bald-faced liar it really ticked me off.

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14. Being right doesn't always feel good.

My mom is a lawyer, who worked a case against one of those "if you or a loved one were negatively affected by this medication" suits. The medication was, in some cases, causing heart issues; important to note, stress can cause heart issues as well. The suit was filed by a slimy law firm, who were telling people that they could win money, even if people were not actually experiencing the side effects. One of these clients had a brain tumor, recently had a nasty divorce, and her son had just died, among all sorts of other terrible luck. Her heart issues did not match the side effects of the medication, and instead looked stress related, so my mom had to cross examine this woman, asking:

"could your inoperable brain tumor be causing you stress?"

"could your divorce from your abusive husband be causing you stress?"

"could the death of your young son be causing you stress?"

That woman's case was dismissed, but my mom felt TERRIBLE.

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13. More bark than bite.

I handle employment cases. We took a disability accommodation case against a regional retail company. To be clear, we were right: our client was not being given a pretty easy accommodation. Normally, demand letters don’t have any real effect. We have stopped sending them to streamline the process and have just started filing with the EEOC or the courts directly. That’s SOP for us.

In this case we followed SOP and filed with the EEOC. The company got in touch with us immediately, expressing horror and regret. The whole thing was one poorly trained manager acting out. While that’s common, companies usually try to cover for the manager and often make things worse. This one did not. They immediately sent him to be retrained, offered the exact accommodation requested, and paid all lost wages and fees, with some extra for emotional distress. Client happily accepted and went back to work.

After seeing the company’s great response, I felt bad for taking them to the EEOC. Not bad enough to start sending time wasting demand letters again, but if I ever see them on the other side, I’ll make an exception.

I almost wish there was no confidentiality provision in the settlement agreement. Would love to say who this was and tell people that they’re a great company. I now prefer shopping with them over their competitors, since I know they’re an upstanding group. Every company messes up sometimes. Not many acknowledge it and try to make it right when they do.


12. Be your own advocate.

Represented someone in the sale of a bar. Buyers of the bar were only buying the business. Most of their free cash was set as a signing payment to the seller, so seller got the cash whether or not the liquor authority approved their license. They allowed the seller to secure the sales contract and the rental agreement for the bar location with a lien on their license and buyers pre-signed an agreement to surrender the license back to seller if they fell behind on payments. Inventory was sold separately. We got buyers to accept tax liability if any for the preceding business. We also told them the seller had only paid themselves in dividends and never cut a paycheck to themselves (buyers were clueless enough to breathe a sigh of relief at this).

Made buyers acknowledge they received the sales agreement 10 days before closing and that we were advising they consult an attorney and an accountant in that time. They didn't. One of the most one sided business deals I've seen.

Buyers came back two months later, and I thought here we go. Nope. They had a disagreement with some investors and wanted me to represent them. Sorry, conflicted out. Business of course failed on down the road and the license went back to the seller.


11. For the greater good.

I helped represent a slumlord in a lawsuit regarding discrimination in public housing based on disability. The state was representing the disabled tenant. The facts were pretty clear, slumlord discriminated on the basis of disability.

Our state doesn’t have much case law regarding discrimination in housing based on disability. So the state was really hoping to get make case law.

We ended up sowing enough doubt to survive the tenants motion for summary judgment. Knowing that the tenant needed money, we made an offer for a decent amount of money for a disabled tenant, but peanuts for the slumlord.

I imagine the state wanted to proceed to trial, but the tenant needed money and accepted. By gaining the best outcome for our client, we allowed the slumlord to get off basically scot-free and deprived our state of needed case law.


10. He gave them every chance.

I defended a death case, representing the insurance company. A man had a brain injury due to a car accident, and died six months later. His family sued my client.

I've never seen a lazier effort on behalf of a Plaintiff. The Plaintiff firm immediately handed the case over to a junior associate. She barely did anything with it. We had settlement negotiations but they were way too high considering the lack of actual medical evidence they had come up with to link the death to the car accident. It probably was related, but you can't walk into court with that argument and no evidence to support it. That seemed to be their plan.

On the eve of trial I told her to accept the settlement but she refused. I told her she would lose because I was going to get all of her "evidence" thrown out. Still, they went to trial.

The partner that was supposed to be there with her didn't show up because his dog was sick. No joke. As I predicted, all of her evidence was thrown out. The family was crying. I won but I didn't feel great about it.

The Judge was appalled. I'm sure the firm was sued for legal malpractice. The young associate was gone within weeks.

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9. Using the law to cry wolf.

As a former prosecutor, I tried a case where a niece (heavily influenced by and through her mom) pressed criminal charges for assault on a female for her uncle kissing her on the forehead.

Mom saw nothing but wanted to testify to present assault statistics, which were inadmissible and not relevant in our case. I wouldn’t put her on the stand and she almost got thrown out of the court room for making a sign out of napkins saying “IT'S MY RIGHT TO TESTIFY.”

Story was Uncle owned the house and would have to abandon it to them if he was deported. Technically an unwanted physical touching is an assault, so we won the case. Fortunately the judge stayed judgment so I believe he was allowed to stay in the country.

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8. Don't commit fraud, even a little.

I’m an in-house attorney for a company a close friend owns. This is a case we “settled,” which was a “win” in our book, but not in the strictest sense. Though, these cases are rarely that straight forward.

The allegations centered around securities fraud, so I engaged outside counsel in securities transactions and baptized myself in the statutes. Said friend is a terrific human, though she dropped the proverbial ball in filing certain securities registrations due to being distracted—her husband was dying of cancer at that time (he eventually died). However, she is an absolute control freak with an ego the size of a fresco, and refused to delegate. This is why she’s in trouble; basically, business negligence that led to a securities violation that looked like fraud.

Now, you don’t have to be malicious to be convicted of fraud, but if the State Securities Commission finds you liable, they can post for the public certain “journalistic” articles expounding upon their latest conquests (or at least, they can in this state). My friend was featured in particularly gruesome articles that slammed her reputation in the ground. She was devastated and became unstable, suicidal, etc.

I settled with the Commission and won many concessions, including a waiver for the hefty fine and dismissal of huge violations for the company. However, she was required to personally accept the fraud allegation, and is barred from certain securities activities for 10 years. Practically, this means that her job prospects and making a living will be severely limited, not just due to her destroyed reputation. She is deeply depressed because of it, even though we “won” on other points. I’ve never seen someone descend into mental and emotional despair and hopelessness as quickly as she did. It’s a sad, horrible and debilitating process to watch.

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7. Learn from your mistakes, much?

In one of my first cases after passing the bar exam, a young man retained me on a DUI. No one was hurt, but he totalled his car. During trial, the arresting police officer testified that my client was clearly inebriated at the accident scene, and that my client was loudly blaming the accident on a mystery person who stole his car, crashed it, and then fled before the cops arrived.

However, according to two other witness statements tendered into evidence, it was my client’s friend (the passenger) who was screaming about someone who stole the car, not my client (the driver).

The cop must have confused the two men during his testimony.

This discrepancy raised a reasonable doubt in the judge’s mind, so she acquitted my client.

At the time, the acquittal was somewhat unexpected for me (in my personal view, my client was clearly at fault and responsible for the accident, regardless of who was blaming the mystery thief to the cops), but I was happy my young client got off, no one was hurt, and lessons were learned. And I was quite euphoric to have won my first criminal case.

The regret? About a month after the acquittal, my young client called me at 3 am from the police station saying “it’s me again! The police arrested me for a DUI again! Can you help me?”

Not only did I answer no, I instantly regretted getting the earlier acquittal. My client apparently didn’t learn any lessons...


6. A near win.

I do juvenile work, criminal law and family law... I represented this client first when he was a juvenile charged with disorderly conduct at school and fighting, then when he became an adult it was for was for simple things like possession of a bit of pot.

As he got older, it became easier and easier to figure out what part of his life hasn’t gone as well as it could and I tried to counsel him and push him to better himself. He got his GED, he started going to NA, he started classes at a community college, and found a part time job.

On the night of his 21st birthday, he was charged with a DWI. Of course I’ll take care of that too. About 6 months later, we are due in court for trial (on a Monday) and he doesn’t show up; which at this point in his life is highly unusual.

As I’m trying to figure out where he is, the court starts going over Arraignments/First Appearances and then low and behold three people are up for Murder charges. The prosecution starts to tell the judge what the facts/circumstances of the case are and mentions a few victims names.

Apparently, my client was at a party when these three individuals decided to allegedly do a drive by shooting. My client suffered multiple gunshot wounds and didn’t make it to the hospital.

So... by default, as you can’t prosecute a dead person; the State has to take a dismissal. I guess technically a win.

Either way, it was crushing to me as I thought he had really turned his life around. (He had.)

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5. Not qualified for help.

Was representing the government at a social benefits tribunal. The applicant was an autistic man who was struggling to make ends meet but was trying his absolute best to contribute everything he could to society. He had a job where his manager was very accommodating and he was a very sympathetic person. He just wanted the extra cash to make his life a little easier for himself. Sadly, he didn't qualify for the benefit, but I think he deserved it. My closing argument was that no matter how much we empathized with this man, no matter how deserving we thought he was, he simply didn't qualify and the tribunal had to apply the law. He was unsuccessful and when I left the building to head back to my office he was just sitting outside on the curb crying. That image has stuck with me for a few years. Pretty heartbreaking, but unavoidable because social benefits are a finite resource. Often, the criteria for qualification are strict. Not everyone can receive it, otherwise there wouldn't be enough to go around. The particular system I was working in was a needs based system. Those with the most severe disabilities met the criteria and I often advocated on their behalf despite the government's initial position if I felt they met the criteria.

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4. Couldn't sink that low.

After law school I had to turn down a criminal defense job offer because my wife got a better offer somewhere else. So basically, I followed her along and was desperate to find something. After three months of fruitless efforts, I would take just about any job that required a JD - whereas literally the only thing I ever wanted to do was criminal defense.

Three months after moving I got an interview for a "real estate litigation" job. They hired me the next day, looking back that was probably red flag number one. First day on the job they taught me how to foreclose on a claim of lien. These are two things I had never heard of before. Turns out, it is totally brainless work if you have the right forms - mind-numbingly boring basically just cutting and pasting new addresses and amounts owed. So anyways, it took me about two months to realize this (when I had my first set of hearings) but literally my sole purpose at the firm (which represented over 100 Home Owners Associations) was to take people's houses away for not paying their Home Owner's Association dues. After my first set of foreclosures, I actually slipped into a pretty legitimate depression. I was getting paid peanuts to drive nearly an hour to work every day to do work I despised on behalf of people I literally could not pretend to care about. The straw on the camels back was when I started signing the foreclosures and realized I was THAT GUY. Ya know? I understand someone has to do the work I guess - there certainly is a lot of money to be made - but it was not for me. I did that job for three months, came home one Friday, and told my wife I'd rather be homeless than go back on Monday.

By some stroke of luck, I started a stellar criminal defense job within two weeks and all of the heartache has 100% been worth it. I've won a lot of cases (you have to redefine winning and losing when doing criminal defense because sometimes even a particularly juicy plea is a win) and never once felt bad about it. For example, I got a guys plea deal cut from 60 years to 15 years for a string of robberies where the interrogations and confessions where overwhelmingly unconstitutional - like, the interrogations were textbook how not to do an interrogation (Missouri v. Seibert) - and stuff like that. Never lost sleep over someone not going to jail.

So yeah, every case where I took someone's house away (probably two dozen times) for not paying HOA fees (generally $4,000 or less) was the worst case I ever won.

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3. Ugh, what a guy.

I'm in family law. Summer of 2018 I get work regarding what seemed, from the client's description, a pretty drawn out and messy divorce case. The husband was my client, and he made it seem, very adamantly, that his soon to be ex-wife was after his every penny. Given he seemed to have a fairly high paying job, it seemed like a pretty common type of case, the city I work in has many instances of this, it has a high cost of living and a lot of well-paid working professionals in private industry. He was a very well spoken, amicable guy in his late 50s, and truly seemed like he'd been taken by surprise and betrayed by his soon to be ex-wife.

When I actually got to the case, however, I was basically floored.

His wife was a working professional as well, worked in government, they'd been married for over twenty years and had two kids together, and a paid off house. Before taxes he made almost three times what she did, not counting his stock options, and yet she'd contributed equally to their mortgage on every home they'd owned over the course of the marriage. By all accounts, despite a vast difference in income, she'd carried her weight, raised two kids, and worked full time during the entirety of the marriage. I live and work in Canada, she could have easily raked him over the coals in the divorce if it had gone to court.

Instead, it seemed like she'd done everything she possibly could to not have him subjected to that. This divorce had been ongoing for five years before he hired me, and it was basically him looking a gift horse in the mouth over and over, a constant renegotiation on the contract they'd both signed initially, with him skimping on alimony and then debating on lesser terms. He was basically given an inch and tried to take a mile, dragging it out for so long that per divorce law it had to go to court. I almost suspect he did so as a way to try and drag her through the mud, though he may have genuinely been that delusional.

I consider it a win only because his ex-wife was adamant about only wanting what was somewhat fair, and for it to be over because of the strain it was having on the family. Per the contract he owed her, still, about 50k in backpay, but she was content with 15k, which was less than this guy made in a month. I did regret the 'win' though, she seemed like a very nice woman with the patience of a saint, while almost all of his anger towards her seemed to come from wounded ego.

ruthson-zimmerman-Ws4wd-vJ9M0-unsplash-300x200.jpgPhoto by Ruthson Zimmerman on Unsplash

2. PO'd at the P.O.

In the spring of 2018, I was a third-year practicing intern at a public defender's office. As the job entailed, I dealt with a lot of clients who were facing time, but none really blew my mind other than the following:

Sometime in that spring, I got up every morning as usual, drove to the office (located in a building with the courthouse), and picked up the files for the for the supervising attorney. I did this because I liked having the exposure with other attorneys whether prosecutors or defense counsel. On this day, a file was scheduled for a probation violation hearing. I looked over the file, and the client had 3 years of probation. I found this very odd due to the initial charge: Possession. Regardless, I thought "another one" because, as awful as it may sound, it really was another one. It wasn't the first PV and wouldn't be the last.

Even so, I go to the docket call, case is called, I say attorney, we move on. In the same room, are POs (their office located floors above the PDs) I go into the holding cell to talk to the client. I ask out, and a white male, 30-35, comes up. I introduce myself, tell him what and who I am, etc. The first words out of his mouth were "$600". I didn't know what that meant or what was going on. So I asked him to find out. What I quickly learned was that this client was mentally impaired; he spoke as if he struggled to form sentences that one may consider coherent and intelligent. During our conversation, he kept bringing up the fact that he didn't do anything, and that he is "paying, paying every month" etc. And, probably due to my lack of experience, I kept trying to steer him towards the issue: Why did he violate his probation conditions? It didn't even cross my mind that, hold on, maybe he did not actually do it.

I left the cell, and talked with the public defender, told him the situation. Sometime later, after handling a few other cases (as you who do it on a daily basis know), we went to talk to him again. This time, I just watched and listened. Immediately upon introducing himself, "$600! I done paid it." Can't shake those words off. Throughout the discussion, the money was being brought up over and over so I decided to figure out what he meant. I went to the clerks, asked for his information. Now I understood: He had fees of over $2000 and all he had left to pay was $600. As probably all of you know, you don't pay, you are in violation. Back in the slammer. So, in his mind, he thought he was there because he wasn't deemed to have paid. The reality was much worse and different.

After a mini investigation, I determined the half-way house, or similar to the idea, he resided. I contacted the wonderful old woman who "ran it" if you will. She gave me details that this man, although he knew, could not regurgitate and express. Turns out his PO was a scum bag. He had gone to the half-way house, told our client what a moron he was and how he was a waste of DNA. He proceed to go into the kitchen, sat down, and brought out his service firearm. Then, he ordered our client to go into the back yard, our client did. PO told him to dig a grave for himself and told him to use the PO's gun to shoot himself in the head. All of this done in front of the old lady. On the day of the case, I called and she immediately came to testify for him.

The judge dismissed the case. Found out later, the PO was doing the same to others and was let go. Never had the chance to meet him face to face. I don't regret winning this case, but I regret the fact that it ever existed in the first place, and probably isn't all that uncommon.

hotrod-die-cast-model-on-board-1422673-300x171.jpgPhoto by Suzy Hazelwood from Pexels

1. This is hardcore.

Third Year law student in a clinic. I came into law school with a very clear moral compass. I knew what I wanted to do (criminal defense) and I had very strong feelings about the death penalty. I thought there was never a situation that warranted it.

Cut to me working in my school's death penalty clinic. The way the clinc worked was that you'd typically be assigned 1-2 clients, review their case, visit them, and do research at the discretion of the supervising attorneys.

I had 1 client, and his case will haunt me for the rest of my life.

Goes in for life after a really brutal assault on a teenager during a burglary. Proceeds to move to more and more secure facilities after numerous guard stabbings and an escape attempt.

But that wasn't what got him the death penalty. See while my guy was in Supermax he managed to slip his cuffs, beat a guard to death with a metal bar, and throw his battered corpse down the stairs.

All of this is on video. There's no question he did it. So the jury deliberates for like a day before they give him the long goodbye.

By the time I get the case it's about reviewing his eligibility for the death penalty. So I dig into his case file for the testimony that appeared at trial and there's all this stuff about huge problems with his cognitive ability and like his actual brain structure.

So, with the supervising lawyer's okay, I do a little independent research, consolidate all the different testimony and map it onto a brain. The conclusion I come to is pretty simple:

This guy has less than half a brain.

Through a combination of substance use, abuse, and birth defects, roughly half of my clients brain just is not present anymore in any meaningful way. Including all the centers that regulate hormone production, fight or flight response, and threat assessment.

I find a bunch of medical reports where people with just some of these conditions get severe behavior imbalances, and in at least 1 case psychotic episodes.

Basically, I help establish that this guy has the kind of diminished capacity that makes him ineligible for the death penalty under Atkins. If he's successful on an Atkins claim then he is structurally ineligible for the death penalty.

But do I feel good about helping to probably save this guys life? No. Because it means he's going to be in a supermax forever and he's already shown that he can kill people in a supermax.

If he doesn't get the death penalty he'll still be in prison for life and I can almost guarantee that he will injure or kill another guard during that time, probably multiple ones.

BUT if he's put to death we're executing someone who really isn't meaningfully responsible for their crimes because most of their brain is gone. He never had the option to make the right decision, or make any decision, because of his incredibly extensive brain damage.

It's out of my hands now, but they are appealing so it's gonna go before the court eventually.

I drank, a lot, that semester and I'll never do death penalty work again.

prison-553836_1920-300x200.jpgImage by Ichigo121212 from Pixabay